Recently I worked together with some Microsoft consultants to implement a Direct Access proof of concept. Initially the configuration went just fine. However, the operational state page showed that we had an issue with the IPSEC certificate. Initially we thought the problem had to do with our DA server being unable to reach the internet in order to download the CRL (Certificate Revocation List). So we had two options: either ask the network team to open up the DA’s external interface connectivity towards the internet or configure the DA server so it could use a proxy.

Due to the workload of the network team, not the best reasoning though, we choose option two: the proxy. We configured the proxy in IE and we were able to successfully download the CRL file. The error didn’t go away though. So we figured we had to configure the system to use the proxy. This can be done using netsh:

netsh winhttp set proxy 10.0.10.30:8080

The error didn’t went away and it was time for lunch so we thought we’d give the DA server a reboot and some time. When we came back there was something weird with the operation state page. It just said Name_Of_DA_Server is not working properly. We tried rerunning the configuration wizard but we got greeted with the following error:

In words: The WinRM client sent a request to an HTTP server and got a response saying the requested HTTP URL was not available. This is usually returned by a HTTP server that does not support the WS-Management protocol. Suddenly we figured out that our netsh winhttp proxy might have broken things a bit. So we gave the command a little twist:

Now that we used this command our DA console was back to normal, but our IPSEC certificate was still in error. The solution was actually quite simple: just make sure the DA server also has a certificate based upon the Computer (or your custom computer) template. Such a certificate can be used for both client and server authentication. This certificate should be issued by the same CA that issues certificates for your clients and that is configured in the DA configuration wizard. After enrolling a certificate we now had a working DA setup. We could see our clients setting up a connection successfully.

One thing that bothered us though: on the operation state page we had an error on the availability of the IPHTTPS interface of the DA server. Now that was odd. netsh showed it as available and after all we had several clients connected to it. When we removed the proxy (netsh winhttp reset proxy) and then the status page went all green!

So for now I’m not even sure if the DA server needs to check the CRL’s of the certificate used by IPHTTPS. But I guess we’ll find out soon if DA stops working. All I can say: the netsh winhttp set proxy doesn’t seems a really good idea to use. Things started breaking in weird and unpredictable ways.

I’m not sure whether there will be another person ever running into this, but if you do I hope this saves you some time.